If you both are in it for the long run, understanding each other's situation won't be that hard. You might not be able to cover the expenses for many reasons. That's understandable But as you've already said, since he is always covering things, at least try not to pick fancy places, even if he can afford it. We as men always want to impress our girls, so he might find it difficult to always choose a regular place. So, that's where you can come in, just pick a random/ your favorite place and try to make it as regular as possible. It doesn't have to be fancy to be funny.